Small head, big thoughts.

Menu

Donald Trump and the “Heads I Win, Tails You Lose” Strategy

When I think of Atlantic City, I think of the Trump Taj Mahal. My family would go down to the shore each summer to visit relatives; every so often, we would find ourselves in Atlantic City. The Taj — a glittering, bombastic, outrageous monument that makes small-scale cultural appropriation look like child’s play — held special appeal for a geography nerd like myself who rarely made it far past the New Jersey suburbs. My aunts and uncles and cousins worked in the casino business, and my grandmother would rack up comps from playing the nickel slots and take my brother, my cousins and me to a big all-you-can-eat buffet in the glittering, smoke-filled halls of the Taj or one of its brethren.

Atlantic City ain’t what it used to be, everyone says these days, and of course it’s true. The Trump Taj Mahal — which no longer has any relation to Trump but bears his name in countless light bulbs and golden letters — is hemorrhaging money and is set to close next month. The number of casinos in town has nearly halved since 2014. Jobs are disappearing; crime is up.

When I visited the area last month, the cover story in the local paper reported on a casino job fair — for casinos in other states who wanted to lure experienced dealers to new facilities in Maryland, New York, and even islands in the Pacific Ocean. “Plenty of casinos are hiring in Atlantic City,” the Press of Atlantic City explained. “But many of the jobs aren’t in Atlantic City.”

Donald Trump, the name and face of Atlantic City at the peak of its glitzy reverie, wants to sever all ties with the struggling city. Atlantic City, in turn, wants to sever all ties with him. When I asked my relatives in the casino industry what they and their colleagues thought of Trump running for president, the response was unequivocal. “The idea of Donald Trump being president is a joke to us,” they said. All he did was take a bunch of other people’s money and run casinos into the ground; the idea of anyone thinking he would be a good president is inconceivable to the people who actually saw him operate.

This finding is neither new nor surprising; plenty of reporters have gone to Atlantic City and drawn similar conclusions. It is interesting only in how it sheds light on the most fascinating part of the Year of the Donald: not his candidacy itself, but in his opponents’ complete disempowerment in trying to combat it.

Trump blunders with unrivaled fecundity, yet emerges relatively unscathed — simply by claiming that he has not blundered at all. If mistakes were made, it was somebody else’s fault. “I made a lot of money in Atlantic City and left 7 years ago, great timing (as all know). Pols made big mistakes, now many bankruptcies,” Trump tweeted.

He claims his bankruptcies in Atlantic City were not errors but shrewd business judgments: like any good businessman, he used the extent of the law to reap reward while pawning off the risk on someone else. If the casinos succeeded, he would have claimed his mantle as a capitalist scion; now that they’ve failed, he instead blames politicians, or the economy, or anything, really, and claims that he somehow succeeded even as everything else fell to shambles.

Like the flip of an uneven coin, Trump has created a system in which there are only two options: heads, he wins; tails, you lose.

I have to admit: I am simultaneously horrified and drawn to the Donald. Reading Donald Trump’s Twitter feed ropes you in like “the Entertainment” in Infinite Jest: once you are sucked in, you are powerless to look away as you slowly rot from within. You read on, doubling down on your bets, telling yourself you will stop when you find something redemptive — yet the tweets just get worse, and all of a sudden you are reading tweets from 2013 and you have already consumed two-thirds of a multi-pound tub of chocolate pudding.

I used to pride myself on not allowing Donald Trump to get under my skin; after all, I am broadly sympathetic with some of the non-racist parts of his populist-leaning agenda (e.g. less foreign intervention, reconsidering the relative merits of global trade deals). Yet something about his recent attempts to undermine the presidential debates and the fairness of the elections crept under my skin. The debates — and voting — are months away, yet he has already insinuated that they are rigged against him. And the liberal Left — myself included — works itself up in a tizzy, because he seems to have caught us in a paradox. What he is saying is obviously absurd, but if the media claims so or tries to “fact-check” him, he is proving their point that they are biased against him. And if they let him run free, he trumpets his successes so highly that the difference between perception and reality slowly loses meaning.

He has pulled the Atlantic City strategy again. Claiming the debates are rigged before they happen — undercutting the platform — makes him powerful. If he performs poorly, he will claim that the moderators and debate format were rigged; the system is conspiring against him. There is no way to prove him wrong, because he is not arguing within the bounds of a shared set of rules. And if the moderators let him off easy, he will extol the unparalleled greatness of his performance. Previously, talking heads and pollsters would determine who “wins” the debate; now, Donald Trump determines who wins. And there are only two options: heads, he wins; tails, you lose.

Last week, he finally acknowledged that President Obama was, in fact, born in the United States, after fanning flames to the contrary for years. But he emerged from the concession as a self-proclaimed winner by blaming others and brandishing his personal heroism. “Hillary Clinton and her campaign of 2008 started the birther controversy,” Mr. Trump said, as quoted in the New York Times. “I finished it.” It doesn’t matter that it’s not true, because he, as an individual, can claim victory, even if he had to fabricate a villain to defeat.

It would be brilliant if it were not so pernicious. Donald Trump has found the loophole to perpetual winning. “We will have so much winning if I am elected that you may get bored with winning,” Trump told a crowd a year ago. He is right, in a way — not because he is actually good at winning, but because he is incredibly talented at destroying the normal mechanisms by which we determine winning and losing. He is Alice in the American Wonderland: up is down, left is right. For Trump, winning is winning, and losing is winning. There is only winning.

In this sense, Trump was wrong: I am not bored. If anything, I am equal parts fascinated and horrified. Fascinated by watching the old boundaries of argument crumble, and horrified by the obvious corollary to winning that will eventually take shape: when Donald Trump can only win, someone else can only lose. As it stands, Donald Trump might be winning, but the taxpayers of New Jersey, the workers in Atlantic City, public discourse, and the Americans who want a fair election are all losing.